Yarn conditioning process and composition therefor



Patented Jan. 10, 1939 v 2,143,765

YARN CONDITIONING PROCESS AND COM- POSITION THEREFOR Joseph B. Dickey and James G. McNally, Roch'ester, N. Y., assignors to Eastman Kodak Comgany, Rochester, N. Y., a corporation of New ersey No Drawing. Application April 26, 1938, Serial No..204,374

. 18 Claims. (Cl. 28-1) This invention relates to the conditioning of lubricating, softening and rendering such yarns textile yarns and more particularly to the conmore amenable to knitting and other textile ditioning of filaments and yarns composed of operations. A furtherand specific object is to organic derivatives of cellulose such as celluprovide a class of conditioning agents which auglose acetate, cellulose propionate, cellulose acement or assist the lubricating action of various 5 tate propionate, and cellulose acetate butyrate, lubricants when applied to such yarns. A still to render them more amenable to textile operafurther object is to provide yarn softening and tions such as knitting and the like. lubricating formulas which can be readily re-.

As is well known in the manufacture of yarns, moved from the yarns by the usual scour baths.

particularly those composed of or containing cel- A still further object is to provide an improved 10 lulose organic derivatives, it is necessary to treat method for the conditioning of yarns, particuthe yarn in order to reduce the tendency toward larly those composed of or containing organic breakage of the individual filaments or fibers derivatives of cellulose such as cellulose acetate,

a when they are subjected to various mechanical whereby the yarn is rendered soft and pliable and strains and to lubricate the yarn in order to capable of employment in a variety of textile V facilitate handling in such operations as spinoperations where complicated designs or stitches ning, twisting, winding. and reeling. It is also are employed. Another. object is to provide an necessary to treat yarn to adapt it for use as improved type of yarn which is especially amenwarp or filling or for the manufacture of various able to textile operations including circular knittypes of knitted fabrics. In knitting, it is parting, weaving, spinning and the like. Other obticllldrly important that the yarn be soft and jects will appear hereinafter. pliable in order that it may conform readily to These objects are accomplished by the followthe contour of the needles and thus produce a ing invention which, in its broader aspects, comclosely knit fabric free from such defects as prises thedis'covery that organic ester amides stitch distortion, pin holes, laddering," and having the general formula: 25

the like. I (Rlx) N (R) OC RH I I Heretofore it has been proposed to employ g softening agents such as polyhydric alcohols and similar agents as ingredients of yarn conditionwhere R is al y cycloalkyl y d ing or lubricating formulas, generally in conare the same or diiferent substituted or unsub- 3o nection with mineral, animal or vegetable oils. Stitllted alkyl, y y a lf p- X 19 It has been found, however, that most of the O-; 12 is 1, bis 1 or more and RX may stand known softening agents and the various formulas for hydrogen, may be used as yarn conditioning containing them have certain drawbacks, one of c agents d pa u rly as softening, a t

the most serious of which is high vapor pressure, with or without the addition of animal, mineral, 35

and in some cases too drastic a solvent action on Vegetable O in t a e t of y ns the yarn. Many of such agents possess slight posed of or containing organic derivatives of or insuificient solvent power for the lubricants cellulose We hav f und that th s compounds with which they are used, and it is accordingly w mp oyed as de r d in t detailed fying agents in order to obtain operable yarn nd/or softening acti n on c llulose r n treating formulas. In addition, many ofth rivative yarns which renders such yarns soft and known softening and lubricating agents are inpliable without at the same time having too sufliciently soluble in water to permit satisfacd c an action thereon tory removal by aqueous scour baths. Typical examples of compounds which, inac- 45 This invention has as its principal object to cordance with our invention, we have found to provide an entirely new class of yarn conditionbe valuable yarn-treating agents are given in ing agents which are particularly adapted for the following table. These compounds which the treatment of yarns composed of or containing may, as indicated above, be considered ester organic derivatives of cellulose and capable OI amides, or more specifically as N,N-di(acyloxy- 50 necessary to employ blending agents or emul iamples set forth below have a slight solvent 40 E alkyl) amides, are derived by reaction on alkylol amines of appropriate acids or anhydrides.

turned to the reaction vessel. The distillation is stopped when 54 parts of water have been 001- Ester amides derivable from monoethanolamine Dimethoxy acetate Ester amides derivable from diethanolamine Compound Formula Boiling range Millimeters 'Iriacetate; CHaCO-N-(CgH OGOCH3); 212-2l4 /23 Diaocetete proplo- C:HCON(C:H OCOCH3)1 220-"225 [23 us a.

'lributyrate C H1CO-N-C2H4OCOCaH1): 220222 l2 2H4OCOCzH5 Acetate proplonate CHaCO-N 240260 I24 butyrate.

CH OCOCaH1J (331E140COCsHL Acetate butyrate CHaO0-N 232-240" caproate.

- CQH4OCOCISH11 Dlbugyrata propi- CzHaCO-N-(Czl-IQOCOCaHfl: 222-230" [23 one e.

Ditproxtlionete bu- C3H1CON-(CaH OCOOH )z 218-225 I22 4 yra e. Tricaproate; 235-245 /2 CzsHuC N- ZH4O 0005 11):

Examples of the preparation of typical compounds of this type are as follows:

Preparation of diethanolamine diacetate propionate cine-000cm CHaC ON C2H4'OCOC2H5' are obtained, boiling at 215-220/23 mm.

Preparation of ethanolamine triacetate Seven equivalents of acetyl chloride are added slowly to two equivalents of ethanolamine. The solution is then refluxed on the water bath until no more hydrogen chloride is given off. The product is then worked up in the usual way; A good yield of the triacetyl derivative is obtained, B. P. 165170/18 mmr Preparation of dietha'nolamine tricaproate One hundred and five parts of diethanolamine, 350 parts caproic acid, 5 parts concentrated sulfuric acid and 100 parts toluene are distilled in such a manner that the toluene is continuously separated from the water of reaction and re-' lected. The catalyst is then neutralized by washing with sodium carbonate solution and the product recovered by distillation. Three hundred and seventy-five parts of the tri-caproyl derivative are obtained, B. P. 235245/5 mm.

Preparation of ethanolamine propionate butyrate Sixty one grams of ethanolamine, 130 grams of propionic anhydride and 160 grams of butyric anhydride are heated under reflux until the reaction is completed. The propionic and butyric acids formed in the reaction are distilled off and the ester-amide is distilled under reducedpressure. The compound'is a colorless liquid and boils at 158-161/11 mm.

In accordance with 'the invention these compounds may be applied directly to the yarn during or after spinning, or may be added to the spinning solution itself. We have found that these compounds have exceptional solvent powers which enable them to dissolve mineral oils and blown and unblown, drying and semi-drying, vegetable and animal oils and accordingly they-may be, and preferably are, employed as ingredients of yarn conditioning or lubricating formulas in I conjunction with agents which function wholly or partially as lubricants.

In the following examples and description we have set forth several of the preferred embodiments of our invention, but they are included merely for purposes of illustration and not as a limitation thereof,

Ourinventlon will be more readily understood by reference to the following examples in which typical applications of the invention are set forth.

This composition is applied to a cellulose acetate 'yarn intended for knitting in an amount representing 4 to 25% by weight of the untreated yarn. The filaments or fibers treated as described above are quite soft and. pliable and give excellent resuits in textile operations, especially in circular knitting.

Other examples of yarn conditioning compositions which may be applied to various types of yarns, particularly those composed of or containing cellulose acetate, cellulose acetate propionate, cellulose acetate butyrate, and similar cellulose organic acid esters in accordance with our invention and which render such yarns soft and pliable and especially well adapted for various textile operations, particularly knitting, are as follows:

Example 3 Cilia-C 80 parts 02 Blown olive oil 20 parts Example 4 CzH4--O C 00H: GHQ-C ON 20 parts I C;Hr-O-C O-C:Hu 7 Light mineral oil 80 parts Example 5 H\ I N-CalEh-O 0 0-013; 20 mm CzlHsC O Blown sperm oil 80 parts Example 6 CHg-O OHrC 0'N(C3Ht0COCH2-0 CH1); 40 parts Neats-ioot oil 60 parts 1 Example 7 Clix-C I I 7 CH: OH-O O-N-(CzH4-O C 0'C Hi): 20 parts CHI-CH1 Sperm oil 60 parts Laurel 20 parts Example 8 C4Hn CHa- C O -N I CH;-CH-CHz-O C 0-0 H; parts (JO-CHa Tetrahydro'furiuryl glycerol acetate 20 parts Blown soya bean oil 80 parts Example 9 Water 80 parts O=CH0-N 10 parts 0 1140 C OC3Ha Water soluble cellulose ester, 5 parts Glymrol acetone 5 parts Example 10 solution of cellulose acetate in acetone in which is incorporated 1-25% by weight of the cellulose acetate, of

is extruded through fine orifices into an evaporative atmosphere. The filaments thus produced are wound or twisted and wound. 'Yarns thus produced are pliable-and suitable for knitting.

For the purpose of conditioning yarns composed of or containing various cellulose derivatives, par-- ticularly the cellulose organic acid esters such as cellulose acetate, cellulose propionate, cellulose acetate propionate, cellulose acetate butyrate and the like, we have found ethanolamine acetate propionate, ethanolamine dibutyrate, ethanolamine propionate-butyrate, and diethanolamine tripropionate to be outstandingly 'efiective. By the use of these compounds we are enabled to produce yarns or filaments having exceptional knitting properties. This is particularly true in the conditioning of yarns for use in circular knitting.

Conditioning liquids which we have found to.

be of particular value in preparing cellulose ester yarns for circular knitting are the following:

Any of the above compositions may beapplied to yarns intended for use in circular knitting by means of a bath, wick, spray, roller, pad or Example 11 I Parts Blown neats-foot oil 15 Ethanolamine propionate'butyrate Example 12 Parts Blown neats-foot oil 20 Ethanolamine propionate butyrate 80 Example 13 Parts Blown olive oil 10-25 Ethanolamine propionate butyrate -75 Example 14 Parts Blown sperm oil -50 Ethanolamine propionate butyrate 5-50 Example 15 t Parts Blown teaseed oil 53-50 Ethanolamine propionate butyrate 95-50 Example 16 Parts Ethanolamine propionate butyrate Example 17 Parts Neats-ioot oil 5-50 Ethanolamine propionate butyrate 95-50 ,Example 18 Parts Blown neats-foot oil 20 'Ethanolamine dibutyrate 80 Example 19 I Parts Blown neats-foot oil 80 Diethanolamine tripropionate 20 Example 20 I Parts Blown neats-foot oil 80 Ethanolamine acetate propionate 20 any suitable means. The amount of condition- 7 As willoe apparent from'the above examples -and: description the: conditioning agents :of our 'ing liquid applied may vary between -25% by" weightof the yarn. Usually, however, the amount of conditioning liquid applied is about -15% by I I weight of the yarn. Yarn composed of cellulose acetate conditioned as described abovegives ex 'celle'nt' results: when used in thecircular knitting process. I

invention may be applied by a wide variety of methods. For example, we may employ the agent 1 as an ingredient of the spinning dope from whichv vulva the filamentsare formed, the amount ofthe' agent so employed depending upon a number of fac-:

tors; such as the particular cellulose derivative used in making the yarn, thesolvent or solvent I 1 combination used in making upthe spinning so-v lution, and the degree I of softness or pliability desired in the yarn, etc.

If the conditioning agent is to be applied to the yarn afterspin'ning, this maybe done by bringing the'yarn in contact with a wick, roll,:'

or felt wet therewith, or the liquid may be applied l ing onto cones, spools, bobbins, or the like or by the SO-Called bobbin to bobbin method. In,

the case of staple fiber'manufacture, the liquid may be applied to the yarn prior to, or after cutting into staple lengths.

to be put and other factors. For example, in a given case where a cellulose Organic acid ester yarn such as a yarn composed of cellulose acetate, is intended for knitting, about 4 to 25% or more by weight, based on the weight .of the dry yarn, may be satisfactory, while if the yarn is intended for weaving, the amount may vary between about 1 and 5%.

Although in the above examples we have referred primarily to yarn treating compositions containing only the conditioning agent and an oil, other ingredients such as solvents, non-solvents, emulsifying agents, blending agents and the like, may be added within the scope of our invention. Likewise, various dyes or other coloring matter may be included in case it is desired to permanently or fugitively tint or dye the material undergoing treatment.

'Although we have found it convenient to illustrate our invention by reference to compositions containing specific percentages of the various ingredients, thesepercentages may vary widely depending upon the particular purpose for which the composition is intended. For example, if it is desired to control the solvent or softening action of the conditioning agent, the amount of formulas described herein are applicable to the conditioning of, many other types of cellulose de-; I rivative yarns such as those composed'of or'con- I I taining cellulose propionate, cellulose butyrate,

cellulose acetate :propionate, cellulose acetatev butyrate, ethyl cellulose, methyl cellulose, benzyl 1 cellulose and others; as wellas to the condition- I ing of silk, wool, cotton, viscose and other natural or artificial materials. 1

The term :yarn? as'used herein and in the claims is'to be understood as including a single the form of a thread, either of high or low twist,

ture of natural and artificial filamentsor a: composite :threadformed by twisting together individual strands of natural or; artificial :materials, I I I as well as, cut staple fibers produced from nat-' 'ural and/or artificialfilaments 01' threads and,

spun yarn'produced from such staple fibers. 1 1

i As indicated: above, thev yarn conditioning agents: of our invention are exceptionally good;

solvents for a wide variety of mineraL'blown and 'unblown, drying and semi-drying animal and. 1 vegetable oils: such as cottonseed, olive, castor, f

neats-foot, sperm and other oils, This enables filament, a plurality of filaments associated: into v "single 'or multiple threads associated or twisted together, composite threads composed of a mix-y up a; variety :of'yarntreating formulas of vary- 'ing'compo'sitionr m: w: I I I I v :tions of ourinvention possess many outstanding advantages"I'he' fundamental and outstanding:

characteristic of the agents employed in accordance with theinventionis their ability to soften yarns, especially those composed of orv containing:

yarn material. Another outstanding characteristic of these compounds is their exceptional solvent power for a wide variety of mineral, animal, and vegetable oils and their ability to act as lubricating assistants in conjunction with these oils when applied to such yarns. In addition, due

,to their solubility'in water, they may be readily removed from yarns and fabrics by means of the usual aqueous scour baths. By employing the yarn conditioning agents and method of our invention as herein described, one is enabled to obtain highly-satisfactory results in the manufacture of yarns and woven fabrics and especially the production from these yarns of closely knit fabrics free from defects such as pin holes, stitch distortion, laddering and the like.

What we claim is: c

l. The process of conditioning yarn to render it more amenable to textile operations including knitting, Weaving, spinning and the like which comprises applying thereto a lubricating and softening composition containing as its essential lubricating and softeningcomponent an organic ester amide having the general formula:

V O a where R is a radical selected from the group consisting of alkyl, cycloalkyl and aryl; R and R" are each a radical selected from thegroup consisting of substituted, and unsubstituted alkyl, aryl and. cycloalkyl; X is CO--; n is l, b is at least 1 and R'X may be hydrogen.

2. The process of conditioning yarn-composed 3.!v I organic derivatives of cellulose such as cellulose acetate and render them soft and; pliable and y amenable; to various textile operations, especiallyl operations such as those involved in weaving and 1 I 1 v knitting where complicated: designs or stitches are 4o employed, without too drastic an action on the where R is a radical selected from the group consisting of alkyl, cycloalkyl and aryl; R and R" are each a radical selected from the group consisting of substituted, and unsubstituted alkyl, aryl and cycloalkyl; X is CO; 11. is 1, b is at least 1 and RX may be hydrogen.

3. The process of conditioning yarn composed of or containing cellulose acetate to render it more amenable to textile operations including knitting, weaving, spinning and the like, which comprises applying thereto a lubricating and softening composition containing as its essential lubricating and softening component an organic ester amide having the general formula:

wherein R is a radical selected from'the group consisting of alkyl, cycloalkyl and aryl; R and R" are each a radical selected from the group consisting of substituted, and unsubstituted alkyl, aryl and cycloalkyl; X is CO; n is 1, b is at least 1 and RX may be hydrogen.

4. The process of conditioning yarn composed of or containing cellulose acetate to render it more amenable to textile operations including knitting, weaving, spinning and the like, which comprises applying thereto a lubricating and softening composition containing as its essential lubricating and softening component an organic ester amide having the general formula:

(RIX),, -N (R) 0 (3' R) v I 0 a where R is a radical selected from the group consisting of alkyl, cycloalkyl'and aryl; R' and R" are each a radical selected from the group consisting of substituted, and unsubstituted alkyl,

aryl and cycloalkyl; X is CO 11. is 1, b is at least l and RX may be hydrogen, and textile lubricant.

5. The process of conditioning yarn composed of or containing cellulose acetate to render it more amenable to textile operations including knitting, weaving, spinning, and the like, which comprises applying thereto a lubricating and softening composition containing as its essential lubricating and softening component diethanolamine tripropionate.

6. The process of conditioning yarn composedv of or containing cellulose acetate to render it more amenable to textile operationsincluding knitting, weaving, spinning, and the like, which.

8. A conditioning agent for rendering y'arns more amenable to textile operations includin knitting, weaving, spinning and the like which comprises an organic ester amide having the general formula:

wherein R is a radical selected from the group consisting of alkyl, cycloalkyl and aryl; R and R" are each a radical selected from the group consisting of substituted, and unsubstituted alkyl, aryl and cycloalkyl;, X is CO; n is 1, b is at least 1 and RX may be hydrogen.

9. A conditioning agent for rendering textile yarns composed of or containing organic derivatives of cellulose more amenable to textile operations including knitting, WeaVing spinning and the like which comprises an organic ester amide having the general formula:

wherein R is a radical selected from the group consisting of alkyl, cycloalkyl and aryl; R and R" are each a radical selected from the group consisting of substituted, and unsubstituted alkyl, aryl and cycloalkyl; X is CO; 11 is 1, b is at least 1 and RX may be hydrogen and a textile lubricating oil.

10. A conditioning agent for rendering yarns composed of or containing cellulose acetatemore amenable to textile operations including knitting, weaving, spinning, and the like containing diethanolamine tripropionate.

1-1. A conditioning agent for rendering textile yarns composed of or containing cellulose acetate more amenable to textile operations including knitting, weaving, spinning, and the like containing ethanolamine acetate propionate.

12. A conditioning agent for rendering textile yarns composed of or containing cellulose acetate more amenable to textile operations including knitting, weaving, spinning, and the like containing ethanolamine propionate butyrate.

l3. Textile yarn amenable to textile operations including knitting, weaving, spinning and the like impregnated with a lubricant containing an organic ester amide having the general formula:

, A I h wherein R is a radical selected from the group consisting ofallwl, cycloalkyl and aryl; R' and R" are each a radical selected from the group consisting of substituted, and unsubstituted alkyl, aryl and cycloalkyl; X is CO; n is 1, b is at least 1 and RX may be hydrogen.

14. Textile yarn composed of or containing organic derivatives of cellulose amenable to textile operations including knitting, weaving, spinning and the like, impregnated with a conditioning agent comprising an organic ester amide having the general formula:

(RX),.N -(R).(O,(|l-R") wherein R. is a radical selected from the group -consisting of alkyl, cycloalkyl and aryl; Rf and R" are each a radical selected from the group consisting of substituted, and unsubstituted alkyl, aryl and cycloalkyl; X is CO; n is l, b is at least 1 and RX may be hydrogen.

15. Textile yarn composed of or containing organic derivatives of cellulose amenable to textile operations including knitting, weaving, spinning and the like, impregnated with a conditioning agent comprising an organic ester amide having the general formula:

( )N(R),. 00-11") ll wherein R is a radical selected from the group consisting of alkyl, cycloalkyl and aryl; R and R are each a radical selected from the group consisting of substituted, and unsubstituted alkyl, aryl and cycloalkyl; Xis CO; n is 1, b is at least 1 and R'X may be hydrogen and a textile lubricant. 16. Textile yarns composed of or containing cellulose acetate amenable to textile operations including knitting,. weaving, spinning and the like, impregnated with a lubricant comprising diethanolamine tripropionate.

17. Textile yarns composed of or containing cellulose acetate amenable to textile operations including knitting, weaving, spinning and the like, impregnated with a lubricant comprising ethanolamine acetate propionate.

18. Textile yarns composed of or containing cellulose acetate amenable to textile operations including knitting, weaving, spinning and the like, impregnated with a lubricant comprising ethanolamine propionate butyrate.

JOSEPH B. DICKEY. JAMES G. MCNALLY. 

